tert-Butyl 4-(2,5-difluoro-4-nitrobenzylidene)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-2,5-difluorobenzyl)piperidine-1-carboxylate

HRID 515308Notes

Reaction equation

HRID 515308 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[C:19]([F:25])=[CH:18][C:3]=1[CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[H][H]>[Pd].C(OCC)(=O)C>[NH2:22][C:20]1[C:19]([F:25])=[CH:18][C:3]([CH2:4][CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)=[C:2]([F:1])[CH:21]=1

Participants

5

Reactant 2

HCID 67193923tert-Butyl 4-(2,5-difluoro-4-nitrobenzylidene)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67194990Tert-butyl 4-(4-amino-2,5-difluorobenzyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-(2,5-difluoro-4-nitrobenzylidene)piperidine-1-carboxylate (4.52 mmol, 1.6 g) and palladium on carbon (10%) (0.135 mmol, 0.144 g) in ethyl acetate was hydrogenated at 3 bar until the desired amount of hydrogen was consumed. The reaction was filtered through celite and concentrated under reduced pressure to give the intermediate tert-butyl 4-(4-amino-2,5-difluorobenzyl)piperidine-1-carboxylate.

Workup

  1. customwas consumed
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f03a9e7aa5394e5bae49c3767c369da8
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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